Dicyclohexylcarbodiimide → HCID 69583678, compound

HRID 1793759Notes

Reaction equation

HRID 1793759 reaction equation
[CH3:1][C@@:2]12[C@H:10](O)[CH2:9][C@@H:5]([C:6]1([CH3:8])[CH3:7])[CH2:4][CH2:3]2.[CH2:12]([CH:15]1[CH2:20][CH2:19][CH:18]([C:21]([OH:23])=[O:22])[CH2:17][CH2:16]1)[CH2:13][CH3:14].C1(N=C=NC2CCCCC2)CCCCC1>ClCCl>[CH2:12]([CH:15]1[CH2:20][CH2:19][CH:18]([C:21]([O:23][C@@H:9]2[CH2:10][C@@:2]3([CH3:1])[C:6]([CH3:8])([CH3:7])[C@@H:5]2[CH2:4][CH2:3]3)=[O:22])[CH2:17][CH2:16]1)[CH2:13][CH3:14]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 1201518[(1S)-endo]-(-)-BorneolHCID 1490324(1s,4r)-4-Propylcyclohexane-1-carboxylic acid

Product 1

HCID 69583678HCID 69583678, compoundYield 21.36%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Example 6 was performed as Example 1 except for substitution of 1.0 g of L-borneol, 1.28 g of 4-n-Propyl-cyclohexanecarboxylic acid, 1.61 g of N,N′-Dicyclohexyl carbodimide (DCC), 0.95 g of N,N-(dimethyl amino)-pyridine (DMAP) and 80 ml of dichloromethane into a round-bottom flask. After filtering and condensing, the residue was subjected to recrystallization from a mixed solvent (CH2Cl2:methanol=1:3), giving (1S,2R,4S)-4,7,7-trimethylbicyclo [2.2.1]hept-2-yl 4-propyl-1-cyclohexanecarboxylate, as a white solid in a 21.36% yield. The optical properties of the resulting compound were tested as in Example 1. The compound exhibited a specific rotation [α] of −22.82 and a helical pitch P of 11.8 μm, with helical twisting power of 8.45 μm−1.

Workup

  1. filtrationAfter filtering
  2. customcondensing
  3. customthe residue was subjected to recrystallization from a mixed solvent (CH2Cl2:methanol=1:3)

Sources & evidence

ORD record
ord-93dfdaf156594f39a8ec8c339b28f7e8
Source dataset
uspto-grants-2006_04
Patent number
US07022259B2

Reaction notes

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